Let's tall about unusual gender bender from the Fate series. Did you know the giant lumberjack Paul Bunyan was a chainsaw toting loli?

>>700
Da Vinci-chan says what we're all thinking.

Honestly, the gender bender usually seen in Fate is pretty boring since the Servants are alternative versions that have no connection to their male equivalents from the real-life myths.
The Fate/Strange Fake LN has some actual gender bender with one of the masters being Francois Prelati(male) who reincarnated himself as a cute girl into modern times and then summoned his old male self as a shota servant. Strange Fake Jack the Ripper also fulfills this fetish to some degree.

>>706
Chevalier d'Éon also was a real life tranny.